


Under the Mask

by TobytheWise



Category: Supernatural
Genre: Dean Winchester Has a Panty Kink, Dirty Talk, Dom Castiel, Domestic, First Meetings, Friends to Lovers, Halloween Costumes, Kinda, M/M, Online Relationship, Panties, Roommates, Sexting, Sub Dean, Two Person Love Triangle
Language: English
Status: Completed
Published: 2018-10-31
Updated: 2018-10-31
Packaged: 2019-08-11 00:58:47
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,264
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16465658
Author URL: https://archiveofourown.org/users/TobytheWise/pseuds/TobytheWise
Summary: Dean's heart is torn. On the one hand, he's been in love with his roommate slash best friend for years. On the other hand, he's about to meet his online Sir for the first time. His heart (and his dick) are conflicted. What could go wrong?





	Under the Mask

**Author's Note:**

  * For [DeadlyKittenKay (PrettyBlueIz)](https://archiveofourown.org/users/PrettyBlueIz/gifts).



> This fic is for Kay written for the ProfoundBond creation exchange. :) I hope you enjoy, friend!! <3

Dean takes a deep breath before clicking on the app, his chat history popping up quickly. He sees that BlueEyedSir has the green dot next to his name, online and waiting for Dean. 

**Are you wearing the panties?**

Dean smiles. His online Sir is very direct which Dean loves. He sends the picture he took while at work today with his pants open, showing off the pink panties underneath. 

**Yes, Sir.**

**Such a good boy for me. So pretty.**

Dean’s face flushes at the praise. His Sir loves to shower him with praise and affections. At first Dean couldn’t handle it. It would make his skin crawl but now he’s grown to let his sink into his skin, grounding him. 

**Thank you, Sir. I always wanna be your good boy.**

**You are. Now I want you to strip for me until you’re down to nothing but your pretty panties.**

Dean removes his work clothes, taking the time to put them in the dirty clothes basket. He snaps the waistband of the panties, groaning at the delicious sting it causes against his skin. What he wouldn’t give for a true, red-inducing spanking from his Sir. The only problem being they’d have to actually know each other in real life.

**Let me see you now, gorgeous.**

Dean takes a picture from the neck down once he’s situated back on his bed. His hard cock straining against the pink lace obscenely. His Sir is going to love this.

**Wow, look at you. So beautiful.**

**Thank you, Sir.**

**Play with your right nipple. Tug it hard. Roll it between your fingers. Make it pink and puffy for me while thinking about my hands on you.**

Dean moans as he touches the nub for the first time. He takes it between his pointer and his thumb, squeezing it hard until it’s pebbled and sensitive. He rolls it between his fingers, picturing his faceless Sir doing it instead. Would his hands be rough from working with his hands, or would they be smooth and gentle? Would he have facial hair to leave beard burn against Dean’s sensitive skin? Would his cock be long and thick, filling Dean up perfectly? Dean’s brought out of his inner musings by the ping on his phone.

**Did you get distracted, gorgeous?**

**Yes, Sir. Sorry, Sir.**

**Pinch your right nipple, for me. Hard. Hold your fingers there until I tell you to let go.**

Dean does as he’s told. His whimpers fill the quiet room as the pain intensifies. He’s squirming by the time his phone pings again, letting him know he can let go. As the blood rushes back to the hard nub, Dean lets out a cry.

**Let go my good boy.**

**Thank you, Sir.**

**Now I want you to reach down into your panties and play with your right ball for me. Tug on it, roll it in your palm.**

Dean again does as he’s told. He starts soft, gently running his fingers against his ball. He moans at the tender feeling of just barely being touched. Then he rolls it in the palm of his hand, back and forth, back and forth. It feels so nice, almost relaxing. Next, he begins to tug on it. He starts gently but quickly begins to tug harder and harder. The pain radiating deliciously through his ball until pleasure is zinging up his spine. He wants more. 

**Do you want more yet?**

**Yes. Please, Sir.**

**I want you to pinch it. Pinch it until it hurts in the way you love. Then tap it before going back to pinching it. Back and forth until you’re right on the edge.**

“Fuck,” Dean whispers breathlessly. His Sir knows exactly how to play him like a fine tuned instrument. He pinches his sac hard until pain radiates through his body, his skin covering with goosebumps as he moans. Once the pain becomes too much be pulls back only to tap his ball. The tap is almost soothing after the stinging pain. His cock drools precome onto his belly as he continues to cycle, stinging, radiating pain and soothing taps. Once he’s right on the edge where one more tap or one more pinch will throw him over the edge, he takes his hand away and picks his phone back up.

**I’m so close to coming. Can I please come, Sir?**

**Not yet, my precious sub. Send me a picture of your beautiful body. Let me see how red your nipple is.**

Dean takes a few deep breaths to help him focus. He raises his camera high enough to get his torso and his lap in the phone. His panties are tucked under his balls so Sir will be able to see everything.

**So fucking beautiful. Look at how you’ve listened so well. One nipple and one ball all nice and red for me. Perfect. You’ll be feeling me for days.**

Dean whimpers into his empty room wishing his Sir was really here to praise him. 

**Go ahead and stroke your cock through your panties. I want you to make a mess of them today.**

Dean tucks his cock back into the panties before wrapping his hand around himself. The silky feel of the panties against his cock has him groaning. His hips jerk up in little aborted thrusts as he drives himself closer to the edge. 

**Such a good boy. Get yourself right to the edge again.**

Dean tightens his grip, stroking from base to tip through the panties. He throws his head back against the pillow as his body floods with pleasure. He quickens his strokes until he’s right on the edge of coming before pulling his hand away and gripping the bed sheet beneath him. “Son of a bitch,” he whispers into the empty room as he picks up his phone. 

**Took myself to the edge again and stopped. My entire body is shaking with need. Please, Sir.**

Dean’s hands shake as he waits for a response from his Sir. He thinks back on the time his Sir made him edge himself over and over again, fucking into a fleshlight while recording himself for his Sir to watch later. 

**Good boy. Now I want you to make yourself come. But you only have five strokes to do it.**

Dean groans, throwing his head back against his pillow. The last time they played this game Dean didn’t get to come because he couldn’t get himself off with only five strokes. This time he’s gotta play smart. 

**May I please play with my hole, Sir?**

Dean waits impatiently for his Sir to respond. His body shifting unconsciously against his sheets, squirming with impatience. 

**I will allow that. But only five strokes, boy.**

**Yes, Sir. Thank you, Sir!**

Dean puts his phone down and reaches for his bottle of lube he left on the nightstand. He covers two of his fingers before moving his panties to the side, swirling his finger against his hole as soon as the material is out of the way. He quickly plunges on finger inside himself, loving the feeling of being stretched.

“Yes,” Dean moans as his second finger enters him. His lust grows higher and higher, wanting to be a good boy and obey this time. But he also just wants to come so fucking bad. 

Dean pinpoints his prostate, driving himself wild by rubbing against the sensitive nub vigorously. But he needs more. With his right hand, Dean snaps the side of his panties against his right ball. It’s the perfect amount of sting over the redden and oversensitive skin. Dean whimpers as he does it three times right after the other. He’s so, so fucking close now. 

A third finger is pressed into his hole. He torments his prostate as he also snaps the panties one more time, the hardest he has yet and he’s right there. Dean wraps his right hand around his hard cock, stroking it three times through his panties before he comes, soiling the pretty pink. He uses his other two strokes to prolong his pleasure before pulling both of his hands off of himself, knowing his Sir wouldn’t want him to do anything more. 

Dean’s cock dribbles the rest of his release and all Dean can do is stare, wishing he could stroke himself for just a little longer. But that’s not his call. He’s not the one in charge.

Dean sends his Sir a picture of his soiled panties.

**I did it, Sir. Thank you.**

**I’m so proud of you, boy. You’re such a good boy for me.**

**Thank you, Sir.**

Dean lays in his bed, staring up at the ceiling once he’s logged off the app. Only two more days he reminds himself over and over again. Two more days and he’ll finally meet the man who’s got Dean completely wrapped around their finger. He’ll finally meet the man who can make him cum harder than anyone before and fill his chest with warmth and affection. Two more days.

~~~

Dean drains the noodles just as Cas walks into the kitchen. Dean’s roommate slash best friend slash the guy that Dean’s been in love with for years. Cas has a giant smile on his face as he peers over Dean’s shoulder, whistling a tune as he goes. 

“Someone’s in a good mood,” Dean comments as he begins to plate their dinner. 

Cas bumps his shoulder with Dean and gives him a giant, gummy smile, the kind that makes Dean’s heart speed up and his knees weak. “I just had a nice chat with an online friend.”

Dean’s chest tightens with a mixture of jealousy and frustration. Because even though he loves Cas, the man he’s known since they shared a dorm room college, he also has some really fucking strong feelings for his Sir. Confliction fills his head but he just shakes it off. For now.

Dean hands Cas a plate. “Ready to eat?”

“I am,” Cas says with a smile as he goes and sits down. Dean follows after him, walking a bit funny so his ball sac doesn’t rub in his jeans the wrong way, causing his mind to flicker back to his Sir. 

_ What am I gonna do? _ he thinks to himself, not for the first time.

~~~

Dean walks out of the dressing room in his short leather shorts, red chest harness, red mask, and red devil horns. He feels incredibly sexy in his outfit and he hopes his Sir will think so too. Now he just needs to find the man dressed as an angel. Shouldn’t be too hard to find in a kink club, right?

Dean’s mind goes to Cas as he begins walking around, looking for a pair of angel wings. He grins at the thought of his straight laced friend being in a place like this. Dean’s not sure the poor guy would even know what to do. 

“Hey, sweetie,” a brunette woman says beside him. “Looking to have some fun tonight?”

Dean’s body tenses as the unfamiliar domme. She’s pretty in her sexy police officer costume but she’s not Sir. Dean politely shakes his head. “No thank you,” he says politely. “I’m actually waiting for someone.”

“Oh really,” she says, putting her hand on his arm. 

“Excuse me,” a low, gravelly voice says from behind Dean. It causes his body to shiver and his face to flush, because he knows that voice! Dean turns with wide eyes finding his roommate and best friend standing behind him. A scowl on his face which is directed at the brunette. “I’d appreciate it if you took your hand off my boy,” Cas growls. 

Dean’s eyes are glued to Cas’ outfit as he glares down the domme that Dean’s already forgotten about. Big white wings are on Cas’ back. He’s dressed as an angel. He’s wearing a blue mask over his eyes just like his Sir told him he’d be wearing. 

“Holy shit,” Dean whispers, voice laced with awe. 

A dark chuckle brings Dean’s eyes back to Cas’. His friend’s lips are curved into a grin as they stare at each other. “This is unexpected,” Cas says carefully, his brow raised. 

“But not unwanted,” Dean states, his face flushing as he looks down at the floor. Strong, long fingers grip his chin and tilt his head back up. 

“You’ll never know how glad I am that it’s you.”

“Really?”

Cas nods. “Can I kiss you?”

“Please,” Dean breathes and suddenly there’s a pair of lips against his. Cas’ lips are chapped but fit perfectly against his. Dean gives Cas control of the kiss straight away, not wanting it any other way. Cas’ hands grip Dean’s waist, holding him exactly how he wants Dean and that little show of dominance has Dean’s cock trying to push its way out of Dean’s tiny leather shorts. 

When they pull away from each other, Cas’ eyes shine with a fiery lust that Dean’s never seen before. “Your choice, boy. Option A. I take you to the room I reserved tonight and give you the treatment I was planning for the person I met online.” Cas takes a step forward until his lips are touching Dean’s ear. He whispers, “or I can take you home and show you all the things I’ve been dreaming of doing to my roommate since we started sharing a room in college.”

Dean swallows before clearing his throat. “The second, Sir. I want you to make me yours. Please.”

Cas gives Dean a fond smile before placing a gentle kiss against his lips. “You’re mine, Dean. From now on, you’re mine.”


End file.
